Diisopropylethylamine → [1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanone

HRID 2362777노트

반응식

HRID 2362777 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O-:19])=O)[CH2:12]1)(=[O:10])=[O:9].[Li+].[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[CH:25]=[CH:26][CH:27]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([N:29]2[CH2:30][CH2:31][CH2:32][CH:28]2[C:24]2[CH:23]=[C:22]([CH3:21])[CH:27]=[CH:26][CH:25]=2)=[O:19])[CH2:12]1)(=[O:9])=[O:10]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 35440982-(3-Methylphenyl)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67131265Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate

생성물 1

HCID 57822305[1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanone수율 23.1%

시약·촉매·용매 2

HCID 22350042dichloromethane N,N-dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution 0.1 g Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate (0.32 mmol) in DMF:DCM (3:1) was added 0.047 g 2-(3-methyl phenyl)-pyrrolidine (0.29 mmol) and 0.27 mL DIPEA (1.6 mmol). The mixture was stirred for 10 minutes at room temperature and 0.147 g HATU (0.38 mmol) was added. The mixture was stirred overnight at room temperature, diluted with 15 mL brine and extracted with ethyl acetate (3×10 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to dryness to obtain the crude product which was further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane to yield 0.03 g (20.8%) of the title compound. (MH+) 447.07.

후처리

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure to dryness
  6. customto obtain the crude product which
  7. customwas further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ebdb94662a104b3695f30cdd3227d7aa
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691846B2

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